100K Vacay midstream check-in and scoring | | Coffee Break Ep73 | 10-7-25

8 snips

Oct 7, 2025

This week, Stephen Pepper, a contestant in the 100K Vacay challenge, shares his travel experiences from London to Munich's Oktoberfest. Despite flight delays, Stephen's highlights include local interactions and brewing beer at the festival. He discusses the replicability of their adventures, while competitor Nick recounts his hike at Caminito del Rey and a missed connection in Madrid. The judges grade their trips on factors like 'Destination Wow' and 'Value,' with both travelers showcasing their unique adventures and clever point redemptions.

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ANECDOTE

London Brew Day Then Oktoberfest Arrival

Stephen and Shay flew JFK–London, spent a day exploring offbeat London, and brewed beer at Brewhouse & Kitchen Highbury.
They then flew to Munich and navigated delays to arrive at Oktoberfest, where they secured a table and socialized with locals.

ANECDOTE

Missed Connection, Cliffwalk, And Windsurfing

Nick flew Boston–Madrid using Amex-transferred Avios, missed his Iberia connection, then rebooked to Malaga and hiked Caminito del Rey.
He stayed at Palacio Silesio using Hilton points and later rented a car to windsurf in southern Spain.

ADVICE

Take The Train To Caminito Del Rey

Do take the commuter train from Malaga to El Chorro rather than booking an expensive tour to reach Caminito del Rey.
The train is cheap and bookable on the rail site and gets you to the shuttle for the walkway cheaply.

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Last week, Greg completed his benchmark trip using 100K Chase Ultimate Rewards points for an incredible vacation in Malta. Shortly after he returned, Tim, Nick and Stephen set out to try and out-shine his trip using 100K of the transferable points they chose to compete with. Unfortunately Tim's trip came to an early end due to an unavoidable need back home, so Nick and Stephen were left to tackle the challenge themselves. With a return deadline by the October 8th 9pm final live check-in, our more than half way finished.

This podcast episode features the full midstream live check-in where we heard trip recaps from both of our competitors and gave out grade scores for how they're doing in each main scoring category so far: Destination Wow, Applicability, Value, and Style.

(00:24) - What is 100K Vacay?

(01:31) - The Peppers summarize their travels so far, from JFK to London to Munich's Oktoberfest

(06:42) - Nick summarizes his trip from Boston to Madrid to Malaga, where he had to rebook his flight from Madrid to Malaga, but then eventually made it to the Caminito del Rey cliffside hike

(15:02) - Is Nick nervous about the budget?

(16:56) - Greg and Carrie assign grades for the "Destination Wow" category for the Peppers

(22:16) - Greg and Carrie assign grades for the "Destination Wow" category for Nick

(25:57) - Greg and Carrie assign grades for the "Applicability" category for the Peppers

(30:00) - Greg and Carrie assign grades for the "Applicability" category for Nick

(32:02) - Greg and Carrie assign grades for the "Value" category for the Peppers

(34:37) - Greg and Carrie assign grades for the "Value" category for Nick

(36:55) - Greg and Carrie assign grades for the "Style" category for the Peppers

(38:55) - Greg and Carrie assign grades for the "Style" category for Nick

(40:02) - That leaves the Peppers just ahead of Nick in every category except for "Style" so far

(41:08) - Budget usage so far

(43:06) - What was the highlight and lowlight for everyone?

(49:34) - Greg, are you surprised everyone flew to Europe?

(53:13) - What's been the biggest obstacle with your bookings so far?

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Music Credit – Beach Walk by Unicorn Heads